Popular Eastern Caribbean Cruises

Family with kids enjoying lying on the sandy beach.

Upcoming Popular Eastern Caribbean Cruises

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A beautiful sailboat rests in the shallow, clear turquoise waters off the coast of Belize City, with lush palm trees and colorful buildings lining the shore.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Eastern/Western Caribbean Adventurer Holiday Cruise

Aboard

Star Princess

From

Fort Lauderdale, Florida

4 Sailings

Dec 13, 2025 - Dec 19, 2026

4 Sailings

Dec 13, 2025 - Dec 19, 2026

Peaceful sunrise over a sandy Florida beach with sea oats in Port Canaveral.

FREE Dining, Waterparks, Entertainment & More*+ 1 more offer

7-night Eastern Caribbean Cruise

Aboard

Mardi Gras

From

Port Canaveral, Florida

57 Sailings

Dec 13, 2025 - May 15, 2027

57 Sailings

Dec 13, 2025 - May 15, 2027

Published prices from

$682

per person*

taxes & fees included

An aerial view of a luxurious resort and pristine sandy beach on the coast of Puerto Plata, Dominican Republic, with turquoise waters, lush green hills, and a cityscape in the background.

75% off 2nd Guest + 3rd, 4th, & 5th Guests Sail FREE + Bonus Savings*+ 2 more offers

7-night Key West, Bahamas & Labadee Cruise

Aboard

Celebrity Apex

From

Port Canaveral, Florida

8 Sailings

Dec 13, 2025 - Apr 18, 2026

8 Sailings

Dec 13, 2025 - Apr 18, 2026

Published prices from

$1,261

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

6-night Exotic Eastern Caribbean Cruise

Aboard

Carnival Magic

From

Miami, Florida

9 Sailings

Dec 13, 2025 - Apr 26, 2026

9 Sailings

Dec 13, 2025 - Apr 26, 2026

Published prices from

$369

per person*

taxes & fees included

A secluded cove with white sand and turquoise water on Half Moon Cay, Bahamas, surrounded by jagged, rocky cliffs and a serene blue ocean under a partly cloudy sky.

FREE Dining, Waterparks, Entertainment & More*+ 1 more offer

6-night Eastern Caribbean Cruise

Aboard

Carnival Vista

From

Port Canaveral, Florida

37 Sailings

Dec 13, 2025 - May 16, 2027

37 Sailings

Dec 13, 2025 - May 16, 2027

Published prices from

$419

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean: San Juan & St. Thomas Cruise

Aboard

Nieuw Statendam

From

Fort Lauderdale, Florida

6 Sailings

Dec 13, 2025 - Mar 28, 2026

6 Sailings

Dec 13, 2025 - Mar 28, 2026

Published prices from

$634

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Eastern/Western Caribbean: San Juan & Mexico Holiday Cruise

Aboard

Nieuw Statendam

From

Fort Lauderdale, Florida

1 Sailing

Dec 13, 2025

1 Sailing

Dec 13, 2025

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

21-night Southern & Eastern Caribbean: Abc & Leeward Holiday Cruise

Aboard

Zuiderdam

From

Miami, Florida

1 Sailing

Dec 13, 2025

1 Sailing

Dec 13, 2025

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

10-night Southern Caribbean: Amber Cove & Abc Islands Cruise

Aboard

Zuiderdam

From

Miami, Florida

2 Sailings

Dec 13, 2025 - Mar 25, 2026

2 Sailings

Dec 13, 2025 - Mar 25, 2026

Published prices from

$1,361

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

8-night Southern Caribbean & Perfect Day Cruise

Ft. Lauderdale

Willemstad

Oranjestad

Perfect Day at CocoCay

Aboard

Oasis of the Seas

From

Fort Lauderdale, Florida

9 Sailings

Dec 13, 2025 - Apr 18, 2026

9 Sailings

Dec 13, 2025 - Apr 18, 2026

Published prices from

$1,059

per person*

taxes & fees included

A sunny, tropical beach on Grand Turk Island with multiple hot air balloons flying over the turquoise water and shoreline.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

5-night Eastern Caribbean Cruise

Miami

Grand Turk

Nassau

Aboard

Freedom of the Seas

From

Miami, Florida

21 Sailings

Dec 13, 2025 - Apr 17, 2027

21 Sailings

Dec 13, 2025 - Apr 17, 2027

Published prices from

$428

per person*

taxes & fees included

FREE Dining, Onboard Activities & More*+ 1 more offer

7-night Southern Caribbean Cruise

San Juan

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

St. Croix

Fort de France

+2 more

Aboard

Jewel of the Seas

From

San Juan, Puerto Rico

19 Sailings

Dec 13, 2025 - Apr 18, 2026

19 Sailings

Dec 13, 2025 - Apr 18, 2026

Published prices from

$709

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

14-night Caribbean East/West Adventurer Holiday Cruise

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

5 Sailings

Dec 14, 2025 - Feb 22, 2026

5 Sailings

Dec 14, 2025 - Feb 22, 2026

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean Cruise With Puerto Rico

Ft. Lauderdale

Princess Cays®

San Juan

St. Thomas (Charlotte Amalie)

Aboard

Sun Princess

From

Fort Lauderdale, Florida

5 Sailings

Dec 14, 2025 - Feb 22, 2026

5 Sailings

Dec 14, 2025 - Feb 22, 2026

Published prices from

$4,024

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

14-night Caribbean East/West Adventurer Holiday Cruise

Ft. Lauderdale

Grand Cayman (George Town)

Aboard

Sun Princess

From

Fort Lauderdale, Florida

3 Sailings

Dec 14 - Dec 28, 2025

3 Sailings

Dec 14 - Dec 28, 2025

A stunning aerial view of the turquoise waters and white-sand beaches around Paradise Island in Nassau, Bahamas, with the Atlantis resort visible in the distance.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean Cruise

Aboard

Carnival Celebration

From

Miami, Florida

88 Sailings

Dec 14, 2025 - Mar 26, 2028

88 Sailings

Dec 14, 2025 - Mar 26, 2028

Published prices from

$534

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 1 more offer

8-night Eastern Caribbean With St. Thomas Cruise

Port Canaveral

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

San Juan

Grand Turk

Aboard

Sky Princess

From

Port Canaveral, Florida

3 Sailings

Dec 14, 2025 - Feb 8, 2026

3 Sailings

Dec 14, 2025 - Feb 8, 2026

A scenic shot of the stunning Seven Mile Beach in Grand Cayman, with a wide, sandy beach, calm turquoise water, and resorts with palm trees under a beautiful blue sky.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

6-night Grand Cayman, Bahamas & Mexico Cruise

Ft. Lauderdale

Key West

Cozumel

Grand Cayman (George Town)

Aboard

Celebrity Eclipse

From

Fort Lauderdale, Florida

6 Sailings

Dec 14, 2025 - Apr 19, 2026

6 Sailings

Dec 14, 2025 - Apr 19, 2026

Published prices from

$733

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

7-night Western Caribbean & Perfect Day Cruise

Miami

Nassau

Perfect Day at CocoCay

Puerto Plata

Aboard

Symphony of the Seas

From

Miami, Florida

10 Sailings

Dec 14, 2025 - Apr 19, 2026

10 Sailings

Dec 14, 2025 - Apr 19, 2026

Published prices from

$954

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Eastern Caribbean: Bahamas & San Juan Holiday Cruise

Aboard

Eurodam

From

Fort Lauderdale, Florida

1 Sailing

Dec 14, 2025

1 Sailing

Dec 14, 2025

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

6-night Western Caribbean Cruise

Aboard

Allure of the Seas

From

Fort Lauderdale, Florida

10 Sailings

Dec 14, 2025 - Aug 2, 2026

10 Sailings

Dec 14, 2025 - Aug 2, 2026

Published prices from

$989

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean & Perfect Day Cruise

Miami

Perfect Day at CocoCay

San Juan

St. Thomas (Charlotte Amalie)

Aboard

Independence of the Seas

From

Miami, Florida

16 Sailings

Dec 14, 2025 - Apr 18, 2027

16 Sailings

Dec 14, 2025 - Apr 18, 2027

Published prices from

$759

per person*

taxes & fees included

An aerial view of a long pier with a red trolley, stretching from the sandy beach of Bimini island to a collection of colorful houses, with clear turquoise water all around.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean: Amber Cove & Bahamas Cruise

Aboard

Eurodam

From

Fort Lauderdale, Florida

6 Sailings

Dec 14, 2025 - Mar 29, 2026

6 Sailings

Dec 14, 2025 - Mar 29, 2026

Published prices from

$584

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 4 more offers

TCW EXCLUSIVE

7-night Tortola, Antigua & Bahamas Cruise

Aboard

Celebrity Beyond

From

Miami, Florida

9 Sailings

Dec 14, 2025 - Apr 19, 2026

9 Sailings

Dec 14, 2025 - Apr 19, 2026

Published prices from

$931

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Virgin Islands & Puerto Plata Cruise

Ft. Lauderdale

Puerto Plata

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Celebrity Xcel

From

Fort Lauderdale, Florida

9 Sailings

Dec 14, 2025 - Apr 19, 2026

9 Sailings

Dec 14, 2025 - Apr 19, 2026

Published prices from

$1,177

per person*

taxes & fees included

Popular Eastern Caribbean Cruises

Upcoming Popular Eastern Caribbean Cruises

14-night Eastern/Western Caribbean Adventurer Holiday Cruise

7-night Eastern Caribbean Cruise

$682

7-night Key West, Bahamas & Labadee Cruise

$1,261

6-night Exotic Eastern Caribbean Cruise

$369

6-night Eastern Caribbean Cruise

$419

7-night Eastern Caribbean: San Juan & St. Thomas Cruise

$634

14-night Eastern/Western Caribbean: San Juan & Mexico Holiday Cruise

21-night Southern & Eastern Caribbean: Abc & Leeward Holiday Cruise

10-night Southern Caribbean: Amber Cove & Abc Islands Cruise

$1,361

8-night Southern Caribbean & Perfect Day Cruise

$1,059

5-night Eastern Caribbean Cruise

$428

7-night Southern Caribbean Cruise

$709

14-night Caribbean East/West Adventurer Holiday Cruise

7-night Eastern Caribbean Cruise With Puerto Rico

$4,024

14-night Caribbean East/West Adventurer Holiday Cruise

7-night Eastern Caribbean Cruise

$534

8-night Eastern Caribbean With St. Thomas Cruise

6-night Grand Cayman, Bahamas & Mexico Cruise

$733

7-night Western Caribbean & Perfect Day Cruise

$954

14-night Eastern Caribbean: Bahamas & San Juan Holiday Cruise

6-night Western Caribbean Cruise

$989

7-night Eastern Caribbean & Perfect Day Cruise

$759

7-night Eastern Caribbean: Amber Cove & Bahamas Cruise

$584

7-night Tortola, Antigua & Bahamas Cruise

$931

7-night Virgin Islands & Puerto Plata Cruise

$1,177

More to Explore

14-night Eastern/Western Caribbean Adventurer Holiday Cruise

7-night Eastern Caribbean Cruise

$682

7-night Key West, Bahamas & Labadee Cruise

$1,261

6-night Exotic Eastern Caribbean Cruise

$369

6-night Eastern Caribbean Cruise

$419

7-night Eastern Caribbean: San Juan & St. Thomas Cruise

$634

14-night Eastern/Western Caribbean: San Juan & Mexico Holiday Cruise

21-night Southern & Eastern Caribbean: Abc & Leeward Holiday Cruise

10-night Southern Caribbean: Amber Cove & Abc Islands Cruise

$1,361

8-night Southern Caribbean & Perfect Day Cruise

$1,059

5-night Eastern Caribbean Cruise

$428

7-night Southern Caribbean Cruise

$709

14-night Caribbean East/West Adventurer Holiday Cruise

7-night Eastern Caribbean Cruise With Puerto Rico

$4,024

14-night Caribbean East/West Adventurer Holiday Cruise

7-night Eastern Caribbean Cruise

$534

8-night Eastern Caribbean With St. Thomas Cruise

6-night Grand Cayman, Bahamas & Mexico Cruise

$733

7-night Western Caribbean & Perfect Day Cruise

$954

14-night Eastern Caribbean: Bahamas & San Juan Holiday Cruise

6-night Western Caribbean Cruise